CA2189558A1 - N-[n-(3,3-dimethylbutyl)-l-.alpha.-aspartyl]-l-hexahydrophenylalanine 1-methyl ester useful as a sweetening agent and method of preparation - Google Patents

N-[n-(3,3-dimethylbutyl)-l-.alpha.-aspartyl]-l-hexahydrophenylalanine 1-methyl ester useful as a sweetening agent and method of preparation

Info

Publication number: CA2189558A1
Authority: CA; Canada
Prior art keywords: aspartame; compound; aspartyl; sweetening; methyl ester
Prior art date: 1994-05-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002189558A

Other languages

English (en)

French (fr)

Inventor

Claude Nofre

Jean-Marie Tinti

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-05-09

Filing date

1995-05-05

Publication date

1995-11-16

1995-05-05 Application filed by Individual filed Critical Individual

1995-11-16 Publication of CA2189558A1 publication Critical patent/CA2189558A1/en

Status Abandoned legal-status Critical Current

Links

235000010357 aspartame Nutrition 0.000 title claims abstract description 43
238000000034 method Methods 0.000 title claims abstract description 20
FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title claims abstract description 6
235000003599 food sweetener Nutrition 0.000 title description 16
239000003765 sweetening agent Substances 0.000 title description 16
150000001875 compounds Chemical class 0.000 claims abstract description 39
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims abstract description 37
108010011485 Aspartame Proteins 0.000 claims abstract description 36
239000000605 aspartame Substances 0.000 claims abstract description 36
229960003438 aspartame Drugs 0.000 claims abstract description 36
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 11
239000003054 catalyst Substances 0.000 claims abstract description 9
LTNUSYNQZJZUSY-UHFFFAOYSA-N 3,3-dimethylbutanal Chemical compound CC(C)(C)CC=O LTNUSYNQZJZUSY-UHFFFAOYSA-N 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
238000001914 filtration Methods 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000002904 solvent Substances 0.000 claims abstract description 5
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims abstract description 4
229910003446 platinum oxide Inorganic materials 0.000 claims abstract description 4
125000003158 alcohol group Chemical group 0.000 claims abstract description 3
229910052697 platinum Inorganic materials 0.000 claims abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 3
238000001704 evaporation Methods 0.000 claims abstract 2
230000008020 evaporation Effects 0.000 claims abstract 2
238000001556 precipitation Methods 0.000 claims abstract 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
238000002156 mixing Methods 0.000 claims description 2
229930006000 Sucrose Natural products 0.000 description 13
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 13
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235000013305 food Nutrition 0.000 description 8
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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238000007126 N-alkylation reaction Methods 0.000 description 3
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159000000007 calcium salts Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
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125000000896 monocarboxylic acid group Chemical group 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000011591 potassium Substances 0.000 description 3
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000004067 bulking agent Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
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235000010980 cellulose Nutrition 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000015218 chewing gum Nutrition 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
238000010586 diagram Methods 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
-1 gums Substances 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
235000014594 pastries Nutrition 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
235000019605 sweet taste sensations Nutrition 0.000 description 2
238000012360 testing method Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
NUFKRGBSZPCGQB-FLBSXDLDSA-N (3s)-3-amino-4-oxo-4-[[(2r)-1-oxo-1-[(2,2,4,4-tetramethylthietan-3-yl)amino]propan-2-yl]amino]butanoic acid;pentahydrate Chemical compound O.O.O.O.O.OC(=O)C[C@H](N)C(=O)N[C@H](C)C(=O)NC1C(C)(C)SC1(C)C.OC(=O)C[C@H](N)C(=O)N[C@H](C)C(=O)NC1C(C)(C)SC1(C)C NUFKRGBSZPCGQB-FLBSXDLDSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000004377 Alitame Substances 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 description 1
108010016626 Dipeptides Proteins 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
108050004114 Monellin Proteins 0.000 description 1
YFONKFDEZLYQDH-OPQQBVKSSA-N N-[(1R,2S)-2,6-dimethyindan-1-yl]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine Chemical compound C[C@@H](F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-OPQQBVKSSA-N 0.000 description 1
101100507983 Pyrococcus furiosus (strain ATCC 43587 / DSM 3638 / JCM 8422 / Vc1) hydG gene Proteins 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
239000004376 Sucralose Substances 0.000 description 1
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
230000032683 aging Effects 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
235000019409 alitame Nutrition 0.000 description 1
108010009985 alitame Proteins 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000010411 cooking Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
235000013365 dairy product Nutrition 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
238000004455 differential thermal analysis Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
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230000014759 maintenance of location Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
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235000019260 propionic acid Nutrition 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
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239000007787 solid Substances 0.000 description 1
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239000008107 starch Substances 0.000 description 1
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235000019408 sucralose Nutrition 0.000 description 1
BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
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239000006188 syrup Substances 0.000 description 1
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235000019640 taste Nutrition 0.000 description 1
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238000012546 transfer Methods 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Peptides Or Proteins (AREA)
Seasonings (AREA)

CA002189558A 1994-05-09 1995-05-05 N-[n-(3,3-dimethylbutyl)-l-.alpha.-aspartyl]-l-hexahydrophenylalanine 1-methyl ester useful as a sweetening agent and method of preparation Abandoned CA2189558A1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9405675A FR2719591B1 (fr)	1994-05-09	1994-05-09	Nouveau composé utile comme agent édulcorant, son procédé de préparation.
FR94/05675		1994-05-09

Publications (1)

Publication Number	Publication Date
CA2189558A1 true CA2189558A1 (en)	1995-11-16

Family

ID=9463025

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002189558A Abandoned CA2189558A1 (en)	1994-05-09	1995-05-05	N-[n-(3,3-dimethylbutyl)-l-.alpha.-aspartyl]-l-hexahydrophenylalanine 1-methyl ester useful as a sweetening agent and method of preparation

Country Status (14)

Country	Link
US (1)	US5773640A (de)
EP (1)	EP0759030B1 (de)
JP (1)	JP3627062B2 (de)
CN (1)	CN1147818A (de)
AT (1)	ATE170872T1 (de)
AU (1)	AU2528495A (de)
BR (1)	BR9507628A (de)
CA (1)	CA2189558A1 (de)
DE (1)	DE69504651T2 (de)
DK (1)	DK0759030T3 (de)
ES (1)	ES2123984T3 (de)
FR (1)	FR2719591B1 (de)
RU (1)	RU2138511C1 (de)
WO (1)	WO1995030688A1 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH11169132A (ja) *	1997-12-15	1999-06-29	Ajinomoto Co Inc	アスパルテームとアスパルテーム誘導体の混晶及びその製造方法
US6692778B2 (en)	1998-06-05	2004-02-17	Wm. Wrigley Jr. Company	Method of controlling release of N-substituted derivatives of aspartame in chewing gum
OA11695A (en) *	1998-06-26	2005-01-13	Ajinomoto Kk	Novel aspartyl dipeptide ester derivatives and sweeteners.
OA11654A (en) *	1998-09-18	2004-12-08	Ajinomoto Kk	N-alkylaspartyldipeptide ester derivatives and sweeteners.
US6844465B2 (en) *	1998-10-30	2005-01-18	Ajinomoto Co., Inc.	Method for preparing highly stable crystals of aspartame derivative
CA2348162A1 (en) *	1998-10-30	2000-05-11	Ajinomoto Co., Inc.	Method for preparing crystal of aspartame derivative excellent in stability
BR9914826A (pt) *	1998-10-30	2001-11-06	Ajinomoto Kk	Processo de cristalização de cristais de éster metìlico de n- [n-(3,3-dimetilbutil)-l-alfa-aspartil] -l-fenilalanina
RU2145869C1 (ru) *	1999-04-30	2000-02-27	Орещенко Андрей Владимирович	Способ антимутагенного воздействия на организм

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1258248A (de) *	1968-07-17	1971-12-22
JPH07636B2 (ja) *	1984-12-17	1995-01-11	三井東圧化学株式会社	Ｎ−ホルミル−α−アスパルチルフエニルアラニンの製造法
FR2719590B1 (fr) *	1994-05-09	1996-07-26	Claude Nofre	Procédé perfectionné de préparation d'un composé dérivé de l'aspartame utile comme agent édulcorant.

1994
- 1994-05-09 FR FR9405675A patent/FR2719591B1/fr not_active Expired - Lifetime
1995
- 1995-05-05 ES ES95919483T patent/ES2123984T3/es not_active Expired - Lifetime
- 1995-05-05 JP JP52872595A patent/JP3627062B2/ja not_active Expired - Fee Related
- 1995-05-05 CN CN95192974A patent/CN1147818A/zh active Pending
- 1995-05-05 AU AU25284/95A patent/AU2528495A/en not_active Abandoned
- 1995-05-05 BR BR9507628A patent/BR9507628A/pt not_active Application Discontinuation
- 1995-05-05 US US08/737,138 patent/US5773640A/en not_active Expired - Fee Related
- 1995-05-05 WO PCT/FR1995/000588 patent/WO1995030688A1/fr not_active Ceased
- 1995-05-05 DK DK95919483T patent/DK0759030T3/da active
- 1995-05-05 EP EP95919483A patent/EP0759030B1/de not_active Expired - Lifetime
- 1995-05-05 AT AT95919483T patent/ATE170872T1/de not_active IP Right Cessation
- 1995-05-05 DE DE69504651T patent/DE69504651T2/de not_active Expired - Fee Related
- 1995-05-05 RU RU96123232A patent/RU2138511C1/ru active
- 1995-05-05 CA CA002189558A patent/CA2189558A1/en not_active Abandoned

Also Published As

Publication number	Publication date
DE69504651T2 (de)	1999-04-08
AU2528495A (en)	1995-11-29
RU2138511C1 (ru)	1999-09-27
DE69504651D1 (de)	1998-10-15
JP3627062B2 (ja)	2005-03-09
EP0759030A1 (de)	1997-02-26
CN1147818A (zh)	1997-04-16
JPH10500403A (ja)	1998-01-13
ATE170872T1 (de)	1998-09-15
WO1995030688A1 (fr)	1995-11-16
FR2719591A1 (fr)	1995-11-10
EP0759030B1 (de)	1998-09-09
US5773640A (en)	1998-06-30
FR2719591B1 (fr)	1996-07-26
DK0759030T3 (da)	1999-06-07
ES2123984T3 (es)	1999-01-16
HK1012407A1 (en)	1999-07-30
BR9507628A (pt)	1997-09-23

Legal Events

Date	Code	Title	Description
2003-05-05	FZDE	Discontinued

Publication	Publication Date	Title
CN1114615C (zh)	2003-07-16	一种制备作为甜味剂的糖精衍生物的改进方法
JP2818032B2 (ja)	1998-10-30	甘味料として有用な新規化合物、およびその製造方法
CA2189558A1 (en)	1995-11-16	N-[n-(3,3-dimethylbutyl)-l-.alpha.-aspartyl]-l-hexahydrophenylalanine 1-methyl ester useful as a sweetening agent and method of preparation
EP0879243B1 (de)	2001-05-30	N-(3,3-dimethylbutyl)-l-aspareginsäure-d-alpha-aminoalkensäure-1-phenyl-1-alkanamide, als süsstoff verwendbar
FR2719592A1 (fr)	1995-11-10	Nouveaux dérivés dipeptidiques utiles comme agents édulcorants.
CA2310760C (en)	2008-02-05	Mixed crystals comprising aspartame and aspartame derivative and process for producing the same
JPS61200999A (ja)	1986-09-05	アスパルチルアラニンの２−ピナニルまたはフエンチルエステル
CA2310761C (en)	2008-02-05	Sweetener compositions containing aspartame and aspartame derivative
CA2245898A1 (fr)	1997-08-14	Acide n-(3,3-dimethylbutyl)-l-aspartyl-d-.alpha.-aminoalcanoique n-(s)-1-phenyl-1-alcanamide utile comme agent edulcorant
MXPA00005681A (es)	2002-02-26	Cristales mezclados que comprenden aspartame y derivados de aspartame y un proceso para la produccion de los mismos
MXPA00005683A (en)	2002-02-26	Sweetener compositions containing aspartame and aspartame derivative